25547-53-9

Upstream product

• 4160-80-9 3-phenylglutaric acid anhydride 
• 7325-50-0 3-phenylpentanedial 
• 128951-26-8 6-Methylsulfanyl-4-phenyl-pyran-2-one 
• 3393-45-1 5,6-dihydro-pyran-2-one 
• 934-56-5 trimethyl(phenyl)stannane 
• 4165-96-2 3-phenylglutaric acid 
• 761366-49-8 5-hydroxy-3-phenyl-valeric acid 
• 624-76-0 Iodoethanol 
• 109299-93-6 3-((E)-3-phenyl-2-propenoyl)-1,3-oxazolidin-2-one 
• 173909-83-6 (3-phenylacryloyl)benzamide 
• 37612-74-1 (E)‐1‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐3‐phenylprop‐2‐en‐1‐one 
• 98-80-6 phenylboronic acid 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 106842-97-1 3-phenylpentanedioic acid monoethyl ester 

Downstream Products

• 69815-04-9 (+/-)-5-Methyl-3-phenyl-1,5-hexandiol 
• 58068-76-1 2-hydroxy-4-phenyltetrahydropyran 
• 114199-69-8 2-ethyl-3-phenyl-5-pentanolide 
• 114199-68-7 2-methyl-3-phenyl-5-pentanolide 
• 61198-49-0 (S)-4-phenyltetrahydro-2H-pyran-2-one 
• 71302-21-1 (4R)-4-phenyltetrahydro-2H-pyran-2-one 
• 790661-97-1 trifluoromethanesulfonic acid 4-phenyl-5,6-dihydro-4H-pyran-2-yl ester 
• 861818-42-0 7-oxo-5-phenyl-hept-2-enoic acid ethyl ester 
• 861818-39-5 7-hydroxy-5-phenyl-hept-2-enoic acid ethyl ester 
• 790661-98-2 (E)-6-(1-ethoxybuta-1,3-dienyl)-4-phenyl-3,4-dihydro-2H-pyran 
• 790662-00-9 5-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one 
• 790662-00-9 5-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-cyclopenta[b]pyran-7-one 
• 188670-33-9 7-Hydroxy-2-methyl-5-phenyl-heptanoic acid ethyl ester 
• 188670-37-3 7-Bromo-2-methyl-5-phenyl-heptanoic acid ethyl ester 

Relevant academic research and scientific papers

CATALYTIC ASYMMETRIC HYDROGENATION OF CYCLIC ANHYDRIDES USING RUTHENIUM(II) CHIRAL PHOSPHINE COMPLEX

Optically active γ- and δ-lactones are obtained by the hydrogenation of five- and six-membered cyclic anhydrides using a Ru(II) complex with chiral phosphine ligand, DIOP, as a catalyst.

New Access Routes to Privileged and Chiral Ligands for Transition-Metal Catalyzed Hydrogen Autotransfer (Borrowing Hydrogen), Dehydrogenative Condensation, and Alkene Isomerization Reactions

A group of transition-metal catalyzed hydrogen moving reactions, encompassing hydrogen autotransfer (HAT; also called borrowing hydrogen, BH), dehydrogenative condensation (DHC) and alkene isomerization, displays high atom economy and relies on widely ava

Tricyclic Sulfoxide-Alkene Hybrid Ligands for Chiral Rh(I) Complexes: The "Matched" Diastereomer Catalyzes Asymmetric C-C Bond Formations

Deprotonation of phenyldibenzo[b,f]tropylidene (8) with LDA/t-BuOK followed by quenching with either diastereomer of inexpensive glucose-based t-Bu-sulfinate (R)- or (S)-11 affords a sulfoxide-alkene hybrid ligand as the diastereomeric pairs (SS,SC)-9/(SS,RC)-10 and (RS,RC)-9/(RS,SC)-10, respectively, which via chromatographic/recrystallization may be separated into the four isomers. The optically pure diastereomeric ligands (SS,SC)-9 and (SS,RC)-10 react with [RhCl(coe)2]2 to form the dinuclear complexes (RS,SC)-11 and (RS,RC)-12, respectively, in which the bidentate ligands coordinate the metal centers through the sulfur and alkene donor functions. These complexes catalyze the conjugate addition of arylboronic acids to cyclic Michael acceptors with enantioselectivities of up to 99% ee. DFT calculations show the preponderant influence of planar chirality of the ligand alkene function. The enantioselectivity switch observed between (RS,SC)-11 and (RS,RC)-12 is explained by the inverted cis-trans coordinations of the substrate molecules in catalytic steps.

Laccase/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO): An efficient catalytic system for selective oxidations of primary hydroxy and amino groups in aqueous and biphasic media

Copper salts/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO) catalytic systems enable efficient aerobic oxidations of primary alcohols but they generally show a reduced reactivity in aqueous medium. Herein, we report an oxidative catalytic system composed of Trametes versicolor laccase and TEMPO, which is able to work in buffer solutions at room temperature using ambient air. Although this catalytic system displays great efficiency in aqueous systems, the addition of methyl tert-butyl ether allows the reduction of TEMPO loading, also enhancing the solubility of hydrophobic compounds. This practical methodology promotes the chemoselective aerobic oxidation of hydroxy or amino groups, leading to interesting organic derivatives such as aldehydes, lactones, hemiaminals or lactams.

Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand

A new catalytic system for the dehydrogenative lactonization of a variety of benzylic and aliphatic diols in aqueous media was developed. By using a water-soluble, dicationic iridium catalyst bearing 6,6′-dihydroxy-2, 2′-bipyridine as a functional ligand, highly atom economical and environmentally benign synthesis of various lactones was achieved in good to excellent yields. Recovery and reuse of the catalyst were also accomplished by a simple phase separation and the recovered catalyst maintained its high activity at least until the fifth run. Copyright

Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates

In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.

Rh-IndOlefOx catalyzed conjugate addition/Heck-type coupling of organoboronics to a lactam or a lactone

Four indole-olefin-oxazoline (IndOlefOx) ligands were synthesized and evaluated in Rh-catalyzed reactions between organoboronics and a lactam or a lactone. In addition to the expected conjugate addition products, the formation of significant amounts of Heck-type products was observed. The scope and limitations of these reactions were investigated.

From diols to lactones under aerobic conditions using a laccase/TEMPO catalytic system in aqueous medium

An efficient catalytic system to oxidize quantitatively aliphatic diols using Trametes versicolor laccase and TEMPO has been developed in aqueous medium. Oxidations have occurred in a non-stereoselective fashion but with complete regio- and/or monoselectivity, obtaining lactones with excellent purity after simple extraction. This catalytic system has been demonstrated to be scalable, compatible with the presence of a variety of functionalities, and also allowed the successful enzyme recycling using a laccase-cross-linked enzyme aggregates (CLEA) preparation.

Rhodium-catalysed enantioselective synthesis of 4-arylchroman-2-ones

The rhodium-catalysed enantioselective 1,4-addition of organoboron reagents to arylidene Meldrum's acids as acceptors, allows convenient access to 4-arylchroman-2-ones with good to excellent levels of enantioselectivity. The use of silyl-protected dioxabo

Rhodium-catalyzed conjugate addition of arylindium reagents to α,β-unsaturated carbonyl compounds

A novel rhodium-catalyzed conjugate addition of indium reagents to electron deficient olefins is reported. The reaction takes place in THF/MeOH at 110 °C using arylindium dichlorides, a rhodium(I)-binap complex as catalyst, and α,β-unsaturated ketones and